AI Summary
5 min readThe Moment Ryan’s Italy Trip Went Sideways
The bunk bed collapsed on his youngest son. Ryan Holiday caught the boy as he fell, but the ladder knocked over his older son, leaving both children cut and bruised. Blood everywhere. The hotel manager came up, looked at the scene, said "Okay, all fixed," and walked out. Holiday stood there stunned. This was not the worst part of the trip.
Fortune Favors the Bold — But Not Always
The episode's organizing idea arrives early, when Holiday connects a famous Latin phrase to the landscape he's standing in. Standing on the Bay of Naples, with Mount Vesuvius visible behind him, he recalls Pliny the Elder's last words before rushing into the eruption of 79 AD to rescue his friend Pomponianus: Fortes fortuna iuvat — fortune favors the bold. The phrase is usually invoked for daring and conquest, but Holiday points out that Pliny used it in service of someone else, not himself. And it didn't save him. He died anyway. "Fortune favors the bold," Holiday says. "It does not guarantee success." Pliny's legacy endures not because he survived, but because he acted.
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What you'll learn
- 1 (03:02) **Part Two of the Rome Trip & Stoic Lessons from Pompeii** - Ryan introduces the second part of the trip, noting that the tour of Pompeii was incredible and provides a series of reflections on what it reveals about human nature.
- 2 (06:27) **The Real Meaning of "Fortune Favors the Bold"** - Standing on the Bay of Naples with Mount Vesuvius in view, Ryan recontextualizes the famous Stoic phrase through the story of Pliny the Elder.
- 3 (08:53) **The Pigeon Incident: A Lesson in Misunderstanding** - Ryan recounts a frustrating moment at a restaurant in Sorrento where a manager yelled at him for feeding pigeons, creating a teachable moment for his kids.
- 4 (12:13) **The Trip Goes Sideways: Food Poisoning in Capri** - The family splurges on a private boat to Capri, but the night before, Ryan wakes up with awful food poisoning, and his youngest son is also hit hard.
- 5 (14:13) **The Bunk Bed Collapse** - The family checks into a supposedly kid-friendly hotel on Ischia that turns out to be a dump, and the top bunk collapses on both of Ryan’s sons.
- 6 (20:57) **The Amazing Hotel & The Sinus Problem** - They escape to a wonderful hotel (QC Spa Roma) and have a great time, but Ryan's youngest son keeps complaining about congestion.
- 7 (24:34) **The Scary Ferry Driver** - On the last day on Ischia, a miscommunication with the ferry driver leads to a tense and scary situation where the driver won't let them out of the car.
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Show Notes
Ryan thought running 50 kilometers through Rome would be the hard part of the family trip to Italy but he was wrong. In today’s episode, he shares how the rest of the trip went completely off the rails and what happened after his family got home that made every travel disaster along the way seem small.
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This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Acc
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